Potassium Carbonate → HCID 178494158, compound

HRID 474822Notes

Reaction equation

HRID 474822 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9].[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28]([CH2:31][C:32]2[C:33](=[O:39])[NH:34][C:35](=[S:38])[NH:36][CH:37]=2)=[CH:27][N:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][S:38][C:35]3[NH:36][CH:37]=[C:32]([CH2:31][C:28]4[CH:29]=[N:30][C:25]([O:24][CH3:23])=[N:26][CH:27]=4)[C:33](=[O:39])[N:34]=3)=[CH:10][C:7]=2[C:8]#[N:9])=[CH:13][C:14]=1[C:19]([F:22])([F:21])[F:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219362445-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracilHCID 677745815-(Chloromethyl)-2-{[4-fluoro-3-(trifluoromethyl)phenyl]oxy}benzonitrile

Product 1

HCID 178494158HCID 178494158, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The same procedure as E63 from 5-(chloromethyl)-2-{[4-fluoro-3-(trifluoromethyl) phenyl]oxy}benzonitrile (198 mg, 0.599 mmol), 5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (150 mg, 0.599 mmol) and K2CO3 (166 mg, 1.199 mmol) in DMF (3 mL), except that the reaction time was prolonged to 1.5 h, to afford the title compound (108 mg, 33.2% yield). LCMS: rt=3.32 min, [M+H+]=544

Sources & evidence

ORD record
ord-f8ae603c2224402f995b657535e3ffb2
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

Loading…